Temperature-induced inversion of elution order in the enantioseparation of sotalol on a cellobiohydrolase I-based stationary phase

Fulde, Katrin; Frahm, A. W.

doi:10.1016/s0021-9673(99)00798-0

Cited by 42 publications

(24 citation statements)

References 32 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…The unusual retention behavior observed for S-propranolol was explained by the high entropy of interaction (>11.6 cal/(mol K)) of this antipode with CBH I which compensates for the positive interaction enthalpy (>1.6 kcal/mol). An interesting reversal of the elution order of the enantiomers of R,S-sotalol at a temperature around 40 • C has been reported by Fulde and Frahm for CBH I-CSPs [152]. A similar phenomenon has been observed by Karlsson's group at 30 • C for another amino alcohol and has been attributed to conformational changes of the pro- tein and/or adsorption of both enantiomers to different sites [106].…”

Section: Protein-based Csps For the Separation Of Basic And Unionizedsupporting

confidence: 66%

Separation of drug enantiomers by liquid chromatography and capillary electrophoresis, using immobilized proteins as chiral selectors

Millot

2003

Journal of Chromatography B

134

View full text Add to dashboard Cite

Section: Protein-based Csps For the Separation Of Basic And Unionizedsupporting

confidence: 66%

Separation of drug enantiomers by liquid chromatography and capillary electrophoresis, using immobilized proteins as chiral selectors

Millot

2003

Journal of Chromatography B

134

View full text Add to dashboard Cite

“…On the other hand, a chiral mobile phase reduces the retention of the solute enantiomer that forms a stronger association with the chiral selector. The major problem with chromatographic separation techniques is that the optimal separation condition is compound specific, 29 which results in time consuming and costly method development steps for each compound. For example, over 1000 chiral stationary phases are commercially available for HPLC, yet there is no clear method to determine which phase will provide the best separation.…”

Section: Introductionmentioning

confidence: 99%

Gas-Phase Chiral Separations by Ion Mobility Spectrometry

et al. 2006

View full text Add to dashboard Cite

This manuscript introduces the concept of Chiral Ion Mobility Spectrometry (CIMS) and presents examples demonstrating the gas phase separation of enantiomers of a wide range of racemates including pharmaceuticals, amino acids and carbohydrates. CIMS is similar to traditional ion mobility spectrometry (IMS), where gas phase ions, when subjected to a potential gradient are separated at atmospheric pressure due to differences in their shapes and sizes. In addition to size and shape, CIMS separates ions based on their stereospecific interaction with a chiral gas. In order to achieve chiral discrimination by CIMS, an asymmetric environment was provided by doping the drift gas with a volatile chiral reagent. In this study S-(+)-2-butanol was used as a chiral modifier to demonstrate enantiomeric separations of atenolol, serine, methionine, threonine, methyl-α-glucopyranoside, glucose, penicillamine, valinol, phenylalanine, and tryptophan from their respective racemic mixtures.

show abstract

“…Other evidence from GC has mainly been reported by Schurig's group [5][6][7][8]. Because of the narrow temperature range used in liquid chromatography (LC), there are only a few observations on temperature-induced inversion of elution order [9][10][11][12]; for example, Pirkle [9] reported this phenomenon when using a brush-type column to separate enantiomers of a phenylethylamine derivative in 1993. The experimental temperature was in the range of -25 to 50°C.…”

Section: Introductionmentioning

confidence: 99%

Reversal of Elution Order between Enantiomers of Binaphthol on an Immobilized Polysaccharide-Based Chiral Stationary Phase

et al. 2011

View full text Add to dashboard Cite

Enantioseparation of 1,1 0 -bi-2-naphthol (BINOL) was performed on an immobilized polysaccharide-based chiral stationary phase (CSP), Chiralpak IA, in the normalphase mode. The effects of polar modifier in the mobile phase and column temperature on retention, enantioseparation, and elution order were investigated. An interesting reversal of elution order for BINOL was observed. When ethanol was used as a polar modifier, R-BINOL was eluted first with marginal enantioseparation. Excellent enantioseparation was obtained when ethanol was replaced by 1-propanol, and S-BINOL was eluted first, this effect being retained with 2-butanol, 1-butanol, 1-pentanol or 1-hexanol as the modifier. When isoamyl alcohol was used, reversal of elution order was again observed, i.e., R-BINOL eluted first with marginal enantioseparation, similar to the case of ethanol. When cyclohexanol and cyclopentanol were used, R-BINOL was still eluted first, but enantioseparation was as good as with 1-propanol as the modifier. This is the first report of large enantioseparation obtained in both elution orders for a given selector/selectant system. A retention model based on stoichiometric displacement theory for retention (SDT-R) was investigated to fit the chromatographic data. The reason for solvent-induced reversal of elution order was elucidated based on a derivation of the retention model. Reversal of elution order for BINOL induced by the content of isoamyl alcohol was also predicted based on the model and confirmed by experiment.

show abstract

Temperature-induced inversion of elution order in the enantioseparation of sotalol on a cellobiohydrolase I-based stationary phase

Cited by 42 publications

References 32 publications

Separation of drug enantiomers by liquid chromatography and capillary electrophoresis, using immobilized proteins as chiral selectors

Separation of drug enantiomers by liquid chromatography and capillary electrophoresis, using immobilized proteins as chiral selectors

Gas-Phase Chiral Separations by Ion Mobility Spectrometry

Reversal of Elution Order between Enantiomers of Binaphthol on an Immobilized Polysaccharide-Based Chiral Stationary Phase

Contact Info

Product

Resources

About